4-Piperidinecarboxylic acid → 1-(5-Boronopyrimidin-2-yl)piperidine-4-carboxylic acid

HRID 626927

反応式

HRID 626927 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:19][CH2:18][CH:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12]1.C(N(CC)CC)C>C(O)C>[B:8]([C:5]1[CH:4]=[N:3][C:2]([N:11]2[CH2:19][CH2:18][CH:14]([C:15]([OH:17])=[O:16])[CH2:13][CH2:12]2)=[N:7][CH:6]=1)([OH:10])[OH:9]

参加物

5

反応物 3

HCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

生成物 1

HCID 899237011-(5-Boronopyrimidin-2-yl)piperidine-4-carboxylic acid収率 60.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

2-Chloropyrimidin-5-ylboronic acid (2.00 g, 12.6 mmol) and isonipecotic acid (1.63 g, 12.6 mmol) were suspended in ethanol (25 mL). Triethylamine (1.78 mL, 12.6 mmol) was added and the mixture was heated at 80° C. for 16 h. The reaction mixture was cooled and concentrated in vacuo to dryness. Water (30 mL) was added and the reaction mixture was swirled until the product completely dissolved. On standing, crystallisation occurred. The mixture was cooled in an ice bath for 30 minutes, then filtered. The resultant solid was washed sparingly with water and dried under suction, then freeze-dried, to give the title compound (1.90 g, 7.6 mmol, 60%) as a white solid. δH (d6-DMSO) 8.60 (s, 2H), 8.06 (br s, 2H), 4.60-4.52 (m, 2H), 3.14-3.02 (m, 2H), 2.60-2.54 (m, 1H), 1.90-1.80 (m, 2H), 1.55-1.39 (m, 2H). LCMS (ES+) 252 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo to dryness
  3. additionWater (30 mL) was added
  4. dissolutioncompletely dissolved
  5. customcrystallisation
  6. temperatureThe mixture was cooled in an ice bath for 30 minutes
  7. filtrationfiltered
  8. washThe resultant solid was washed sparingly with water
  9. customdried under suction
  10. customfreeze-dried

出典と根拠

ORDレコード
ord-fb916736a0044af3bdda5eab0620f97b
出典データセット
uspto-grants-2016_04
特許番号
US09309243B2

関連ノート

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